3-Carboxy-phenylisocyanat | 46118-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-Carboxy-phenylisocyanat
• 英文别名: 3-Isocyanatobenzoic acid
• CAS: 46118-13-2
• 化学式: C₈H₅NO₃
• mdl: MFCD06208303
• 分子量: 163.133
• InChiKey: BJVHZTKZQWVAKG-UHFFFAOYSA-N

物化性质

• 沸点：
  324.6±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Carboxy-phenylisocyanat 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 50.5h， 生成 3-(3-{1-Hydroxy-3-[1-hydroxy-1-phenyl-meth-(Z)-ylidene]-2-oxo-2,3-dihydro-1H-indol-6-yl}-ureido)-benzoic acid
  参考文献：
  名称：

  Use of a Pharmacophore Model To Discover a New Class of Influenza Endonuclease Inhibitors

  摘要：

  Data from both our own and literature studies of the biochemistry and inhibition of influenza virus endonuclease was combined with data on the mechanism of action and the likely active site mechanism to propose a pharmacophore. The pharmacophore was used to design a novel structural class of inhibitors, some of which were found to have activities similar to that of known influenza endonuclease inhibitors and were also antiviral in cell culture.

  DOI：

  10.1021/jm020334u
• 作为产物：
  描述：

  三光气 、 间氨基苯甲酸 以 乙酸乙酯 为溶剂， 生成 3-Carboxy-phenylisocyanat
  参考文献：
  名称：

  设计和合成 1H-吡咯并[2,3-b]吡啶衍生物作为 FLT3 抑制剂用于治疗急性髓系白血病

  摘要：

   [显示省略]

  DOI：

  10.1016/j.bmc.2024.117631

文献信息

• Synthesis and AMPA receptor antagonistic activity of a novel 7-imidazolyl-6-trifluoromethyl quinoxalinecarboxylic acid with a substituted phenyl group and improved its good physicochemical properties by introduced CF3 group
  作者：Yasuo Takano、Futoshi Shiga、Jun Asano、Wataru Hori、Tsuyosi Anraku、Takashi Uno

  DOI：10.1016/j.bmcl.2004.07.093

  日期：2004.10

  We describe the synthesis, physicochemical, and biological properties of a novel series of 7-imidazolyl-6-trifluoromethyl quinoxalinecarboxylic acids with a substituted phenyl group attached through a urethane linkage at the C-7 position. We found that the introduction of trifluoromethyl group at the C-6 position brought about good biological activity and physicochemical properties. Among them, compound

  我们描述了一系列新的7-咪唑基-6-三氟甲基喹喔啉羧酸的合成，物理化学和生物学特性，这些取代羧酸具有通过C-7位置的氨基甲酸酯键连接的取代苯基。我们发现在C-6位引入三氟甲基带来了良好的生物活性和理化性质。其中，具有4-羧基苯基的化合物9k（KRP-199）在体外具有对AMPA-R的高效力和选择性，并且在体内具有良好的神经保护作用。此外，该化合物表现出良好的理化性质，例如对光的稳定性和在水溶液中的良好溶解性。
• New potent calcimimetics: I. Discovery of a series of novel trisubstituted ureas
  作者：Taoues Temal、Hélène Jary、Marielle Auberval、Sarah Lively、Denis Guédin、Jean-Paul Vevert、Pierre Deprez

  DOI：10.1016/j.bmcl.2013.01.078

  日期：2013.4

  Starting from Fendiline and R-568, we identified a novel series of urea compounds as positive allosteric modulators of the calcium sensing receptor (CaSR), as part of a program to identify novel therapeutics for secondary hyperparathyroidism. Initially identified disubstituted ureas were converted to trisubstituted urea lead 20e, which was further modified to increase in vivo potency. Replacing a carbomethoxy

  从芬迪林和R-568开始，我们确定了一系列新型尿素化合物，作为钙敏感受体（CaSR）的正变构调节剂，作为鉴定继发性甲状旁腺功能亢进症新疗法的计划的一部分。最初鉴定出的二取代尿素被转化为三取代尿素铅20e，并对其进行了进一步修饰以提高体内效力。用各种生物等位基因取代碳甲氧基取代基导致化合物46在口服给药后表现出有效的体外和体内活性。
• Design and syntheses of hyaluronan oligosaccharide conjugates as inhibitors of CD44-Hyaluronan binding
  作者：Xiaowei Lu、Xuefei Huang

  DOI：10.1007/s10719-015-9597-3

  日期：2015.10

  Hyaluronan (HA) is an integral component of the extracellular matrix. Its interactions with a cell surface receptor CD44 has been shown to play important roles in a variety of biological events including cell proliferation and metastasis. As multivalent CD44-HA binding is critical for downstream signaling, compounds that can selectively disrupt the complex formation of HA polysaccharide with CD44 can serve as useful probes of CD44 mediated cellular events as well as potential leads for novel therapeutics. Herein, we report the synthesis of several series of HA conjugates to target the HA binding pocket of CD44. As a small library of HA disaccharide derivatives failed to exhibit any inhibitory activities, we focused on HA tetrasaccharide based analogs. Traditional synthetic strategies towards HA oligosaccharides involve the construction of backbone from the corresponding monosaccharide building blocks, which can be quite tedious. In order to expedite the synthesis, we designed a new synthetic route taking advantage of the ability of hyaluronidase to generate large quantities of HA tetrasaccharide through digestion of HA polysaccharides. The HA tetrasaccharide obtained was utilized to prepare multiple S-linked HA analogs bearing aromatic groups at the reducing end glycan. One such compound containing an m-benzyl phenyl moiety exhibited significant inhibition of CD44-HA binding. Our approach provides a new direction towards the design of HA based CD44 antagonists.

  透明质酸 (HA) 是细胞外基质的组成部分。它与细胞表面受体 CD44 的相互作用已被证明在包括细胞增殖和转移在内的多种生物事件中发挥重要作用。由于多价 CD44-HA 结合对于下游信号转导至关重要，因此能够选择性破坏 HA 多糖与 CD44 复合物形成的化合物可以作为 CD44 介导的细胞事件的有用探针以及新型疗法的潜在先导物。在此，我们报告了几个系列的 HA 缀合物的合成，以靶向 CD44 的 HA 结合袋。由于HA二糖衍生物的小型文库未能表现出任何抑制活性，因此我们专注于基于HA四糖的类似物。 HA 寡糖的传统合成策略涉及从相应的单糖结构单元构建主链，这可能非常繁琐。为了加快合成速度，我们利用透明质酸酶消化HA多糖产生大量HA四糖的能力，设计了一条新的合成路线。获得的HA四糖用于制备多种在还原端聚糖上带有芳香基团的S-连接HA类似物。一种含有间苄基苯基部分的此类化合物表现出对CD44-HA结合的显着抑制。我们的方法为基于 HA 的 CD44 拮抗剂的设计提供了新的方向。
• Novel urea derivatives, method for preparing same, use thereof as medicines, pharmaceutical compositions and novel use
  申请人：——

  公开号：US20040053925A1

  公开（公告）日：2004-03-18

  The invention relates to new products of formula (I): 1 in which: Y represents oxygen or sulphur, Z represents C═CH2, CH—CH3 or CH2, R1 represents hydrogen, morpholinyl or the 2 radical. In which the two nitrogen atoms are linear or form a cyclic radical, X represents carbonyl, alkylene or alkenylene, linear or branched, containing at most 6 carbon atoms optionally interrupted by oxygen or sulphur, R4, R5 and R6 represent hydrogen, a protective group of the nitrogen, alkyl, cycloalkyl, aryl and arylalkyl optionally substituted, R2 represents alkyl optionally substituted by aryl, heteroaryl or —NR4R5, R3 represents alkyl, cycloalkyl, aryl, heteroaryl, arylalkyl or heteroarylalkyl optionally substituted, these products being in all isomer forms and the salts, as medicaments.

  本发明涉及一种新的化学物质，其化学式为(I)： 其中： Y代表氧或硫； Z代表C═CH2、CH—CH3或CH2； R1代表氢、吗啡啶基或2个氮原子线性或形成环状基团； X代表羰基、线性或支链烷基或烯基，含最多6个碳原子，可选地被氧或硫中断； R4、R5和R6代表氢、氮的保护基、烷基、环烷基、芳基和芳基烷基，可选地被取代； R2代表可选地被芳基、杂环芳基或—NR4R5取代的烷基； R3代表可选地被取代的烷基、环烷基、芳基、杂环芳基、芳基烷基或杂环芳基烷基； 这些化学物质以所有异构体形式和其盐的形式作为药物。
• 5-(Tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-<i>c</i>]pyrimidine-Based Potent and Selective CCK₁ Receptor Antagonists:  Structure−Activity Relationship Studies on the Substituent at N2-Position
  作者：José M. Bartolomé-Nebreda、Rosario Patiño-Molina、Mercedes Martín-Martínez、Isabel Gómez-Monterrey、M. Teresa García-López、Rosario González-Muñiz、Edurne Cenarruzabeitia、Miriam Latorre、Joaquín Del Río、Rosario Herranz

  DOI：10.1021/jm010813d

  日期：2001.6.1

  To establish structure-activity relationships a new series of analogues of the highly potent and selective CCK1 receptor antagonist (4aS,5R)-2-benzyl-5-(N-Boc-tryptophyl)amino-1,3-dioxoperhydropyrido[1,2-c]-pyrimidine (1a) modified at N2-position of the central scaffold has been prepared and evaluated as CCK receptor ligands. With this aim the N2-benzyl group has been replaced by methyl, cyclohexyl, aromatic groups, 1-phenylethyl, and 1-carboxy-2-phenylethyl group. Then, substituents with different electronic and steric properties were introduced into different positions of the phenyl group of analogues 19a and 19b. The results of the CCK receptor binding and in vitro functional activity evaluation suggest the importance of the lipophilic character and an appropriate spatial orientation of the moiety linked at the N2-position of the 1,3-dioxoperhydropyrido[1,2-c]pyrimidine template for potent and selective binding and antagonist activity at CCK1 receptor subtype. The 2-cyclohexyl and (2S)-1-naphthyl derivatives 18a and (2S)-20a have emerged as more potent and selective CCK1 receptor antagonists than the lead compound 1a. Additionally, the results confirm the (4aS,5R)stereochemistry at the central bicyclic skeleton as an essential structural requirement for potent binding to this receptor subtype.